Ammonium Chloride → HCID 21837610, compound

HRID 1739838Notes

Reaction equation

HRID 1739838 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([S:8][C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][O:14][C:15]3=[O:18])=[CH:11][C:10]=2[N+:19]([O-])=O)[S:6][CH:7]=1)[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:19][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[S:8][C:5]1[S:6][CH:7]=[C:3]([CH2:1][CH3:2])[N:4]=1)[C:15](=[O:18])[O:14][CH2:13]2

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 21837615HCID 21837615, compound

Product 1

HCID 21837610HCID 21837610, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 6-(4-ethyl-2-thiazolylthio)-5-nitro-3H-isobenzofuran-1-one (750 mg, 2.33 mmol), Fe powder (600 mg, 10.7 mmol) and NH4Cl (150 mg, 2.8 mmol) in 45 mL of EtOH:H2O (2:1) was refluxed for 1.5 h. The hot mixture was filtered through celite and the celite was washed several times with hot EtOH:THF (4:1). Solvent was evaporated in vacuo and the residue was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated. The solid title compound so obtained was used without purification in the next step.

Workup

  1. temperaturewas refluxed for 1.5 h
  2. filtrationThe hot mixture was filtered through celite
  3. washthe celite was washed several times with hot EtOH:THF (4:1)
  4. customSolvent was evaporated in vacuo
  5. customthe residue was partitioned between H2O and EtOAc
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-54009d1e88144ba8b48178df21f88d11
Source dataset
uspto-grants-1999_10
Patent number
US05968958

Reaction notes

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